Reacción #486706

Ecuación de reacción

(4R)-1-(tert-butyloxycarbonyl)-4-hydroxy-L-proline

triphenylphosphine

p-nitrobenzoic acid

diethyl azodicarboxylate

→

desired product

Rendimiento 77.0%

(4S)-1-(tert-Butyloxycarbonyl)-4-(p-nitrobenzoyloxy)-L-Proline tert-Butyl Ester

Rendimiento 77.0%

Disolventes

benzene

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroevaporated
2. 2
   LavadoFlash silica gel chromatography eluting with 0.5% methanol/dichloromethane

Procedimiento

To a solution of (4R)-1-(tert-butyloxycarbonyl)-4-hydroxy-L-proline (500 mg, 1.74 mmol) in benzene (20 mL) were added triphenylphosphine (548 mg, 2.09 mmol), p-nitrobenzoic acid (349 mg, 2.09 mmol), and diethyl azodicarboxylate (364 mg, 2.09 mmol). The reaction mixture was stirred for 1 hour at 80° C. and then evaporated. Flash silica gel chromatography eluting with 0.5% methanol/dichloromethane gave the desired product in 77% yield (581 mg). 400 MHz 1H NMR (CDCl3): δ1.38-1.47 (3s, 18H); 2.37 (m, 1H); 2.49-2.61 (m, 1H); 5.53 (m, 1H); 8.16-8.27 (m, 4H, Ar).

Fuente